Rhodium-Catalyzed Asymmetric Addition of Arylboronic Acids to β-Phthaliminoacrylate Esters toward the Synthesis of β-Amino Acids
作者： Takahiro Nishimura , Jun Wang , Makoto Nagaosa , Kazuhiro Okamoto , Ryo Shintani
DOI: 10.1021/JA909642H
关键词:
摘要: Rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to β-phthaliminoacrylate esters took place efficiently give high yields β-aryl-β-amino acid with 96−99% enantioselectivity, which was realized by use a hydroxorhodium/chiral diene complex.
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Jun-An Ma, Recent Developments in the Catalytic Asymmetric Synthesis of α- and β-Amino Acids Angewandte Chemie International Edition. ,vol. 42, pp. 4290- 4299 ,(2003) , 10.1002/ANIE.200301600
Manfred T. Reetz, Dominique Moulin, Andreas Gosberg, BINOL-based diphosphonites as ligands in the asymmetric Rh-catalyzed conjugate addition of arylboronic acids. Organic Letters. ,vol. 3, pp. 4083- 4085 ,(2001) , 10.1021/OL010219Y
Ming-Jin Fan, Gao-Qiang Li, Yong-Min Liang, DABCO catalyzed reaction of various nucleophiles with activated alkynes leading to the formation of alkenoic acid esters, 1,4-dioxane, morpholine, and piperazinone derivatives Tetrahedron. ,vol. 62, pp. 6782- 6791 ,(2006) , 10.1016/J.TET.2006.04.100
Stephen G. Davies, Andrew W. Mulvaney, Angela J. Russell, Andrew D. Smith, Parallel synthesis of homochiral β-amino acids Tetrahedron-asymmetry. ,vol. 18, pp. 1554- 1566 ,(2007) , 10.1016/J.TETASY.2007.06.008
Timothy Noël, Koen Vandyck, Johan Van der Eycken, Some new C2-symmetric bicyclo[2.2.1]heptadiene ligands: synthesis and catalytic activity in rhodium(I)-catalyzed asymmetric 1,4- and 1,2-additions Tetrahedron. ,vol. 63, pp. 12961- 12967 ,(2007) , 10.1016/J.TET.2007.10.034
Norihito Tokunaga, Yusuke Otomaru, Kazuhiro Okamoto, Kazuhito Ueyama, Ryo Shintani, Tamio Hayashi, C2-Symmetric Bicyclo[2.2.2]octadienes as Chiral Ligands: Their High Performance in Rhodium-Catalyzed Asymmetric Arylation of N-Tosylarylimines Journal of the American Chemical Society. ,vol. 126, pp. 13584- 13585 ,(2004) , 10.1021/JA044790E
Takahiro Nishimura, Yoshitaka Ichikawa, Tamio Hayashi, Naoya Onishi, Masashi Shiotsuki, Toshio Masuda, Asymmetric Polymerization of Achiral Arylacetylenes Giving Helical Polyacetylenes in the Presence of a Rhodium Catalyst with a C2-Symmetric Tetrafluorobenzobarrelene Ligand Organometallics. ,vol. 28, pp. 4890- 4893 ,(2009) , 10.1021/OM9003797
Zhi-Qian Wang, Chen-Guo Feng, Ming-Hua Xu, Guo-Qiang Lin, Design of C2-symmetric tetrahydropentalenes as new chiral diene ligands for highly enantioselective Rh-catalyzed arylation of N-tosylarylimines with arylboronic acids. Journal of the American Chemical Society. ,vol. 129, pp. 5336- 5337 ,(2007) , 10.1021/JA0710914
Jean-François Paquin, Christian Defieber, Corey R. J. Stephenson, Erick M. Carreira, Asymmetric synthesis of 3,3-diarylpropanals with chiral diene-rhodium catalysts. Journal of the American Chemical Society. ,vol. 127, pp. 10850- 10851 ,(2005) , 10.1021/JA053270W
Mukund P. Sibi, Kalyani Patil, Enantioselective radical reactions. Evaluation of nitrogen protecting groups in the synthesis of β2-amino acids Tetrahedron-asymmetry. ,vol. 17, pp. 516- 519 ,(2006) , 10.1016/J.TETASY.2006.01.018